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10 Tips and Tricks on How To Ask Someone Out

Struggling to figure out how to ask someone out? We’ve got tips for all sorts of situations that will get you closer to your yes.
Editorial team
December 20, 2023
June 20, 2024
min. read
Table of Contents

Whether you're a virgin who can't drive or a self-proclaimed slut who’s all over town, we can all agree that the idea of being alone can feel nerve-wracking and scary. But asking someone on a first date can be even scarier. 

The anticipation of asking someone out often manifests as anxiety, and what should be excitement becomes cold-blooded dread. But crushing on someone is a positive thing. It feels good to like a person, and retaining an air of levity helps you feel more confident.

But just saying that often isn't enough to curtail those anxious thoughts. So if you're a hot, sexy ball of anxiety, like many other homos who wear their hearts on their sleeves, then this one’s for you. We'll show you how to transform yourself from a wallflower into a blossoming rosebud with tips and tricks for asking out your crush. 

We'll even break it down into separate instructions for asking someone face-to-face or via text — two very different playing fields that require unique approaches. Ready? Class is in session, so put on some chapstick and start taking notes.

Do you feel the love tonight? When to ask someone out

They say timing is everything, and they're absolutely right. Spontaneous romance is rare, but Hollywood would have you think you need to wait for the right moment when everything falls into place. 

There is some truth to this; obviously, you should seize the advantage when an opportunity presents itself. But you’ll have to make the magic yourself far more often.

That means hanging out with them, taking an interest in their life, and, yes, actually initiating the conversation. You can’t expect them to put in all the legwork. However, if you play your cards right, you might learn how to get someone to ask you out first.

How to ask someone out in person

It's time to face your fears, take a deep breath, and dig deep for that courage we know you have inside you! Here are tips for asking someone out face-to-face while ensuring you save face:

Assertiveness is sexy — aggression isn't

There is a vast difference between asking someone out on a date and bullying them into having a coffee with you. Lots of people like a bold man, but it only takes a few particular words and the wrong body language to suggest the latter over the former.

It sounds counterintuitive, but anxiety is often the reason we come on too strong. Take some deep breaths, maintain eye contact, and shake off the jitters before you express your feelings. 

Focus on being assertive with that courage you're accessing. Don't be too pushy, and give the person space as needed. Once you've asked, the ball is in their court, so you've already done what you can. There's no need to wilt and hide in a corner once you've asked them out, but you should let them digest the question on their terms.

Don't call it a date

You don't always know how someone will take the big D. (That stands for “date,” obviously.) It can sometimes dissipate the initial awkwardness if you allude to going out without directly saying it. 

Try these lines: 

  • "Hey, wanna grab lunch with me sometime?"
  • "I'd love to treat you to a drink."
  • "I'd love to hang out more and get to know you." 

No big D, no big deal. It can ease everyone’s nerves if you keep things squarely in the talking stage. Plus, you can often gauge a person's interest from this interaction without feeling the outright rejection of someone saying they don't want to date you.

Be a different D word: Direct

This tip for how to ask someone out on a date is for those who are crushing on a particularly dense cutie. Some people aren't going to take the hint when you mildly suggest a hangout, and you'll want to be a bit clearer with them. 

Make your intentions known so they can tell you theirs. If you want to split the difference between this tip and the last one, ask them out for dinner. It’s a decidedly more romantic rendezvous than casual coffee. They’ll (hopefully) get the idea.


Take one on the chin

It doesn't matter who you are: Rejection can happen when you take the plunge and ask someone out. But that's not a bad thing! You know your value, and it's okay if someone you barely met can't see that. 

If you get a “no” from your potential person, bow out and be kind. There's no point in trying desperate gestures to change their mind — this never comes across as anything but a big, vibrant red flag.

And friendship isn't so bad, either. If you like this person, spinning rejection into something positive can alleviate awkwardness and pave the way for a different relationship.

Be specific

Many dates never happen because someone suggests something fun without any follow-through. Don’t ask if they want to get together sometime; ask if they're free Saturday at 7 pm to grab tapas. 

Being specific can prevent this gray area where a million other bits of correspondence must happen for the date to manifest. Plug in the information of where, when, and why, and you're much more likely to get a clear response.

How to ask someone out over text message

Not to be outdone by the terror of asking someone out in person, texting lets you overthink every word until you’re paralyzed with fear. How do you send something that won't be left on read? Start with these tips:

Keep it light

If you’re wondering how to ask someone out in a cute way, sending The Iliad every morning isn’t our top recommendation. Keep your conversations light, humorous, and maybe even a bit saucy. Still, we recommend avoiding anything overtly sexual unless the precedent has already been set.

Find a good balance between flirty and funny: This is a precursor to dating, after all, not a tight five at your local watering hole.

Give them space

Waiting for a response is inevitably stressful. But practice giving space by waiting for your crush to text you back first. It’s our best advice on how to ask someone to hang out without sounding needy. 

This isn’t about playing games; it's about assessing a situation to see if it's worthwhile to continue. Granted, it doesn't always mean they don't like you if they don't text you as much as you text them. But any healthy relationship relies on two people being themselves first, and giving room during text conversations can help set that precedent.

Be unique

Originality in your text convos will help you build intrigue, even if it doesn't help you secure a date immediately. Say what's on your mind, ask them some fun questions, and phrase average things in a way they haven't heard before.

Know when to ask

Nobody is in the mood for a date when they’re in the weeds during a dinner rush. Respect the person's schedule and try not to send potentially stress-inducing text messages when they're busy. And sending it too late at night might give them the impression you're only here for sex.

Take time to get to know them

Learn more about your person. What are they passionate about? What's going on in their life? Ask genuine questions that tell them you care about getting to know their personality. 

Be warned: This can backfire if it goes on too long. If all you're doing is texting back and forth about your lives, momentum can stall, and your window of opportunity might close. There's no easy way to say when this could happen, so trust your gut and go for it if the timing seems right.

Stay true to you and keep searching

The best tip is both obvious and annoying: Be yourself. Sure, these tips and tricks might help you secure that first date. But if they don't feel like something you'd do organically, you’re just reading from a script for a role that isn’t you. 

And take this approach on your date, too. You can read about how to act for a perfect date, but you should be yourself if you really want to connect with that special someone. Otherwise, they’re falling for someone who isn't truly you, and who has time for that? 

Ready to try out some of these tips yourself? You can get some practice on Grindr. Download the Grindr app now and get started!

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